Celebrities Who Almost Got Married

Photo: Disney/Rex/Shutterstock.
At the risk of sounding like the second-best song from Dirty Dancing, love is strange. Throw fame into the mix and all hell is bound to break loose. Celebrities meet, fall in love, and pop the question in a romantic proposal they'll later have their publicists leak to Us Weekly. Sometimes it all ends up happily ever after. Sometimes it ends in divorce. Sometimes it doesn't even make it down the aisle, culminating in tears and magazine covers with two headshots slashed by the jagged line of heartbreak. It's like The Bachelor, times a million.
While Liam Hemsworth and Miley Cyrus' rekindled romance is a reminder that we should never give up hope on our favorite lovebirds, it's almost mind-boggling to consider some of the famous folks who went through a proposal, flashed a ring, contemplated growing old together, and maybe even went to Williams-Sonoma and registered for some Le Creuset. Like, Julia Roberts and Kiefer Sutherland could have been grandparents by now. Nicole Kidman very nearly became her Big Little Lies costar Zoë Kravitz's stepmom. More alarmingly: Guys, we almost missed out on Zigi and TomKat.
It's hard to imagine these stars picking out china patterns and debating the merits of chocolate ganache over cream cream cheese icing, but they almost certainly did — before it all went wrong, anyway. But hey: Don't cry because it's over; smile because it happened.
Read These Entertainment Stories Next:
1 of 34
Photo: Getty Images.
Cameron Diaz & Jared Leto

The title of "hottest couple of the early aughts" goes to Cameron Diaz and Jared Leto, who dated from 1999 to 2003. The pair got engaged in 2000, but never made it down the aisle. Diaz eventually married Good Charlotte rocker Benji "The Twin Who's NOT Married To Nicole Richie" Madden in a 2015 ceremony attended by Leto's own mother, Constance. Her ex remains single, simply waiting for us to cash in on our long-standing Jordan Catalano crush.
2 of 34
Photo: Getty Images.
Evan Rachel Wood & Marilyn Manson

Try to keep up with this one. In between relationships with future ex-husband Jamie Bell (they started dating in 2005, broke up in 2006, got back together in 2011, got married in 2012, had a baby in 2013, and — deep breath — separated in 2014), Wood very nearly became the second Mrs. Marilyn Manson. The Westworld actress was just 18 when she began dating the rock star in January 2007, which resulted in her starring in his video for "Heart-Shaped Glasses." They briefly split up in November 2008, then reunited and announced their engagement in early 2010. The couple broke up for good that November.
3 of 34
Photo: Getty Images.
Lenny Kravitz & Nicole Kidman

The Big Little Lies actress, now happily married to country singer Keith Urban, confirmed that she once almost wed Kravitz, which would have made her costar Zoe Kravitz's stepmother. She dated the rocker around 2003-2004, after her divorce from Tom Cruise.
4 of 34
Photo: Eugene Adebari/REX/Shutterstock.
Kiefer Sutherland & Julia Roberts

The only "designated survivor" in this relationship was Jason Patric, who famously ran off to Ireland with Roberts when she bailed three days before her 1991 wedding to Sutherland. Runaway Bride: not just a film.
5 of 34
Photo: BEI/REX/Shutterstock.
Laura Dern & Jeff Goldblum

No lie: Dern and her Jurassic Park costar almost got hitched in the mid-'90s.
6 of 34
Photo: Rex/Shutterstock.
Gwyneth Paltrow & Brad Pitt

Long before Brangelina and conscious uncoupling, Gwyneth Paltrow and Brad Pitt were peak couple goals. The Seven costars broke off their engagement in 1997 after three years of dating. The split caused a huge media sensation and inspired some choice quotes in 1998's Can't Hardly Wait.
7 of 34
Photo: American Photo Syndicate AA/REX/Shutterstock.
Jamie Walters & Drew Barrymore

How do you talk to a (Charlie's) Angel? Former '90s heartthrob Jamie Walters (The Heights, Beverly Hills, 90210) found out when he popped the question to Drew Barrymore in 1992. The couple split the following year.
8 of 34
Photo: PETER BROOKER/REX/Shutterstock.
Jennifer Lopez & Ben Affleck

Yes, we're all still reeling from the demise of Bennifer 2.0, but let's take a beat to pour one out for the O.G. version. Lopez and Affleck's 2-year-relationship (2002-2004) spanned two terrible movies (Gigli and Jersey Girl), the greatest music video of all time ("Jenny from the Block"), and a postponed 2013 wedding that never ended up happening. Fortunately for Affleck, Daredevil costar Jennifer Garner was standing by (literally).
9 of 34
Photo: BEI/Rex/Shutterstock.
Alanis Morissette & Ryan Reynolds

Oh sure, we've got all the dirty little details about Uncle Joey's sex life, but what happened between Alanis Morissette and her other famous ex remains a bit of a mystery. What we do know is that the Canadian stars began dating after meeting at a party thrown by Drew Barrymore in 2002, were engaged two years later, and split in 2007. At least we'll always have this deleted Just Friends scene in which Alanis calls Ryan an asshole.
10 of 34
Photo: Kevin Mazur/Wireimage; Ron Galella/Wireimage.
Johnny Depp & Jennifer Grey

Settle in: Johnny Depp is on this list A LOT. One of the actor's many famous former love interests was Dirty Dancing star Jennifer Grey, to whom he got engaged in 1989. She did always have a thing for Johnnys.
11 of 34
Photo: Matt Baron/BEI/REX/Shutterstock.
Lance Armstrong & Sheryl Crow

The cyclist was once strong enough to be Crow's man... for a little while. The former couple got engaged in September 2005 after two years of dating, but it all came crashing down just a few months later.
12 of 34
Photo: Gregory Pace/BEI/Rex/Shutterstock.
David Moscow & Kerry Washington

Here's a Scandal: Olivia Pope almost tied the knot with the kid from Big. The actors called time on their 2-year engagement in 2007, long before Shonda Rhimes came knocking on Washington's door.
13 of 34
Photo: Gregory Pace/BEI/REX/Shutterstock.
Mary-Louise Parker & Jeffrey Dean Morgan

Sadly, a love of middle names couldn't keep these once-engaged Weeds stars together. They announced their breakup in April 2008.
14 of 34
Photo: Matt Baron/BEI/REX/Shutterstock.
Darren Aronofsky & Rachel Weisz

The Black Swan director and the British actress were a couple for nearly a decade before ending their engagement in 2010; their son Henry is almost 11. Weisz went on to marry Daniel Craig just a few months after the split, while Aronofsky is currently dating Jennifer Lawrence.
15 of 34
Photo: Matt Baron/BEI/REX/Shutterstock.
Jude Law & Sienna Miller

So nice, they tried it twice. Law's affair with his children's nanny broke this golden couple up for the first time in 2006. They eventually reunited in 2009, only to split in early 2011. Anyone up for Round 3?
16 of 34
Photo: Jim Smeal/BEI/REX/Shutterstock.
Big Sean & Naya Rivera

Long before she succumbed to the charms of David Spade, Rivera only had eyes for Big Sean. She and the rapper announced their engagement in October 2013, but split about six months later.
17 of 34
Photo: Disney/REX/Shutterstock.
Zayn & Perrie Edwards

It was match made in X Factor heaven, but it wasn't to be. Zayn and the Little Mix singer broke off their 2-year engagement not long after his surprise exit from One Direction in 2015. To think, we came so close to never knowing Zigi.
18 of 34
Photo: BEI/REX/Shutterstock.
Marilyn Manson & Rose McGowan

Yep, him again. In 2001 Manson and the former Charmed star broke up after three years, at which point he almost immediately began dating Dita Von Teese, whom he would later end up marrying and divorcing. "There is great love, but our lifestyle difference is, unfortunately, even greater," McGowan said of the relationship during a 2015 appearance on Watch What Happens Live.
19 of 34
Photo: BEI/REX/Shutterstock.
Josh Brolin & Minnie Driver

The actors were altar-bound for a hot minute in 2001. Driver later admitted that Brolin's stepmother, the legendary Barbra Streisand, was "frankly, the best part of our relationship."
20 of 34
Photo: Jim Smeal/BEI/REX/Shutterstock.
Robin Wright & Ben Foster

Foster is now engaged to and expecting a baby with Orange in the New Black's Laura Prepon now, but it's not his first affaire de cœur with a Netflix star. The Hell or High Water actor and the House of Cards actress ended their on-off engagement for good in 2015.
21 of 34
Photo: MediaPunch/Rex/Shutterstock.
Ruby Rose & Phoebe Dahl

The Orange is the New Black actress got engaged to fashion designer (and granddaughter of children's author Roald Dahl) Phoebe Dahl in 2014, but they parted ways in December 2015. Rose is now dating singer Jessica Origliasso of The Veronicas.
22 of 34
Photo: Matt Baron/BEI/REX/Shutterstock.
Tara Reid & Carson Daly

It was a millennium match made in MTV heaven, but it didn't last. Reid and Daly began dating after meeting on the set of Total Request Live in 2000, but called off their wedding in June 2001. Daly doesn't appear to regret that decision. "To some extent, I dodged a bullet," he told Elle in 2012. "I was getting serious about my career, and she wanted to shoot movies and just party in her time off. That didn't work for me."
23 of 34
Photo: Alan Berliner/BEI/REX/Shutterstock.
Johnny Depp & Winona Ryder

In all honesty, we could still see Captain Jack Sparrow and Joyce Byers being an item. Depp got "Winona Forever" inked on his arm, but his relationship with his Edward Scissorhands costar only lasted about three years.
24 of 34
Photo: Matt Baron/BEI/REX/Shutterstock.
Mark Ronson & Rashida Jones

The man behind "Uptown Funk" used a crossword puzzle to pop the question in 2003, but they broke off the engagement about a year later. "We were too young to be engaged and we both were very nervous about it; it felt like a very big, adult step," the Angie Tribeca star later told Elle. "Neither of us were ready and we didn't really deal with it face-to-face and the relationship deteriorated."
25 of 34
Photo: BEI/REX/Shutterstock.
Jeanne Tripplehorn & Ben Stiller

Stiller spoke about his split from the Big Love and Basic Instinct actress, whom he dated for more than five years, in a 1998 Rolling Stone interview. They both married other people in 2000.
26 of 34
Photo: BEI/Rex/Shutterstock.
Dan Aykroyd & Carrie Fisher

According to tributes paid to the late writer and actress after her death last December, she and Aykroyd fell in love while filming 1980's The Blues Brothers. He gave her a ring, but she ultimately decided to get back together with Paul Simon, whom she eventually married (and divorced).
27 of 34
Photo: Dave Allocca/StarPix/REX/Shutterstock.
Joe Manganiello & Audra Marie

Before falling for now-wife Sofía Vergara, the Magic Mike star was engaged to TV personality and model Audra Marie. Manganiello proposed during an Italian vacation in 2010, but the relationship ended the following year.
28 of 34
Photo: Broadimage/Rex/Shutterstock.
Rob Kardashian & Blac Chyna

The Rob & Chyna saga spawned an E! reality show, the birth of Dream Kardashian, and so much drama. To recap: Rob Kardashian is the older half-brother of Kylie Jenner. Kylie Jenner was dating Tyga. Tyga has a son with Chyna. Things got weird.
29 of 34
Photo: Cannon/REX/Shutterstock.
Demi Moore & Emilio Estevez

Way back in 1986, Wisdom costars Moore and Estevez planned to get married. Then they broke up, and she met Bruce Willis. Happily, they kept things amicable, with Estevez directing his former bride-to-be in 2006's Bobby.
30 of 34
Photo: CHRIS PIZZELLO/AP/REX/Shutterstock.
Katie Holmes & Chris Klein

Ever wonder what might have happened if Katie Holmes had married longtime boyfriend Chris Klein instead of Tom Cruise? She ended her engagement to the American Pie actor in early 2005, just weeks before stepping out with Cruise and unleashing TomKat onto the world. We all know how that ended.
31 of 34
Photo: MARK HUMPHREY/AP/REX/Shutterstock.
Billy Bob Thornton & Laura Dern

Please enjoy this 1999 photo of then-lovebirds Laura Dern and Billy Bob Thornton with country singer Travis Tritt. Thornton famously ran off and married Angelina Jolie while still engaged to Dern, whom he dated from 1997 to 1999. Dern's pal Melissa Etheridge, incidentally, was not impressed.
32 of 34
Photo: Kin Cheung/AP/REX/Shutterstock.
Mariah Carey & James Packer

The pop diva and her billionaire beau had a very public breakup last fall after getting engaged in January 2016. You can't keep Mimi down, though.
33 of 34
Photo: Jim Smeal/WireImages; ABC Photo Archives/Getty Images.
Johnny Depp & Sherilyn Fenn

Our final Depp dating detail is his past engagement to Twin Peaks star Fenn in the mid-'80s. Further randomness: She also dated Prince.
34 of 34
Photo: Matt Baron/BEI/REX/Shutterstock.
Evan Peters & Emma Roberts

Honestly, it's hard to keep track of when these actors are on and when they're off. The Liam and Miley of the Ryan Murphy universe appear to be engaged again after rekindling their romance last year.